


Little Red and the Big Bad

by NavajoLovesDestiel



Category: Supernatural
Genre: Alternate Universe, Anal Fingering, Anal Sex, Bottom Castiel, College AU, Dean/Cas Tropefest 5k Mid-Winter Challenge, Fluff, Halloween Costumes, Love, M/M, Smut, Top Dean
Language: English
Status: Completed
Published: 2018-04-15
Updated: 2018-04-15
Packaged: 2019-04-23 10:10:56
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 3,439
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14330214
Author URL: https://archiveofourown.org/users/NavajoLovesDestiel/pseuds/NavajoLovesDestiel
Summary: Dean glimpses a sight of a guy dressed as little red riding hood at his frat's Halloween party, and it just so happens he is dressed as the big bad wolf. But when red disappears, he is frantic to find the guy of his dreams.





	1. Chapter 1

**Author's Note:**

> I really want to thank my friend and editor, QuillsAndInk!

 

 

Dean was pretty excited about the Halloween party. It was being held at his frat house for the first time since he’d been at the University of Kansas and it was going to be epic. He chose his costume carefully, opting to go as a wolf.

He wandered downstairs once the party was in full swing. He kind of wanted to make an entrance and he’d taken his time to get his costume just right.

He went to the kitchen to grab a beer. He didn’t want to get blitzed too early. He cruised the rooms, checking out all the amazing costumes.

Then he noticed the guy in the very naughty little red riding hood costume. The guy was standing against a wall, nursing a beer and watching everyone.

Dean’s stomach did a flip. What he could see of the guy’s face was gorgeous and the fact that he was wearing red fishnet thigh-highs, a very short skirt, a skin-tight red top and a red hoodie amazed Dean. The guy obviously wasn’t concerned about what anyone else thought.

Dean slid up next to the guy and smiled.

“Hey there, Red. You’re looking very pretty tonight.”

The guy turned to look at Dean and his blue eyes sparkled behind the mask.

“Oh, Mr. Wolf. What big eyes you have.”

Dean grinned. “All the better to see you with, Red.”

The guy smiled. “And Mr. Wolf. What big teeth you have.”

“All the better to chew that skirt right off you.”

The guy giggled. “You don’t seem to know the story very well.”

Dean leaned over and whispered in the guy’s ear, “I forgot how it went when I saw how hot you look in that outfit. So tell me, are you wearing red panties as well?”

The guy took a long sip of his beer.

“Well of course I am, Wolfy. How could I wear anything else?”

Dean bit his lower lip. “Show me, Red.”

The guy laughed merrily and turned around, lifting his skirt to show Dean his panty-clad ass for a brief second.

Dean was entranced.

“My name is Dean. Dean Winchester.”

The guy giggled. “Hi Dean, I’m Red.”

Dean touched the guy’s cheek. “Come on. Tell me your name.”

The guy tipped up the last of his beer. “Get me another beer, and I will.”

Dean hurried to the kitchen, grabbing two beers. When he got back, the guy was gone.

He looked around and asked everyone if they knew the guy in the red riding hood costume. No one did. Dean ran out the door, looking up and down the street. There was no sign of him anywhere.

“What the fuck?” Dean’s night was ruined. .

In the days to follow, Dean looked everywhere he went on campus, looking for any guy who looked like he might be Red.

A couple of weeks passed with no luck. Dean was beginning to think the guy didn’t even go to this college.

Exactly one week later, Dean had to go to the library. Dean needed to find a book for a paper he was writing. He was wandering the stacks, when someone caught his eye.

The guy putting books back on the shelves had a body that matched Red’s to a tee. He walked up next to the guy, and when the guy turned around, those startling blue eyes got wide.

Dean grinned. “Red? I’ve been looking for you ever since you ran away from me at the party.”

The guy smiled and it lit up the room.

“Well, hello, Wolfy.”

“Why did you take off on me like that? And what’s your name?”

“Cas. Cas Novak and I left because I don’t do one night stands.”

Dean smirked. “You think that’s all I wanted?”

Cas shook his head. “Oh, come on. You were looking at me like I was dinner. You wanted to fuck me into the mattress and then send me on the walk of shame.”

Dean stared at Cas for a beat.

“Well, I admit I wanted to fuck you. Come on, you were dressed in a slutty red riding hood outfit. But you don’t know me. I wouldn’t have sent you on any walk of shame. I would have made you breakfast and walked you home in the morning.”

Cas snorted.

“I’ll prove it to you if you’ll let me. Let me take you out for a burger and a beer after you get off work.”

Cas took a beat, thinking.

“Okay’ You’re on, Winchester. I get off at six.”

Dean smiled brightly. “Great! I’ll be here at five till, and thanks, Cas.”

Cas went back to work and Dean went off to find his book.

At exactly five till six, Dean walked in. Cas looked up from behind the front desk and smiled.

“Right on time. I like that in a date.” Cas turned to the guy standing next to him. “I’m leaving, Kevin.”

Dean walked them to his car. Cas whistled when he saw it. “Nice car, Dean.”

Dean grinned and ran his hand down the fender. “Thanks. This is my baby.”

Cas smirked. “It must have been a difficult birth.”

“Ha ha, Novak. Get in.”

 

*****

 

They sat in a booth, talking, and drinking their beers while they waited for their food to arrive.

Cas found out that Dean was a psych major.

“Interesting. What do you want to be when you grow up?”

Dean grinned. “I never intend to grow up, Cas, but I want to do forensic psychology.”

Cas was impressed and he said so.

“What’s your major, Cas? Let me guess… acting?”

Cas laughed. “Not quite. Major in English, minor in creative writing.”

“So you want to write the great American novel?”

Cas took a swallow of his beer. “Something like that.”

“So, what made you decide to be red riding hood?”

Cas looked at him. “Seemed like the thing to do. I enjoy dressing up like a woman.”

Dean’s mouth dropped open. “You’re into crossdressing?”

Cas looked sly. “Yeah, sometimes. You didn’t seem to mind at the party.”

“Fuck. I don’t mind now.”

“Got a kink, Winchester?”

“Yeah, I do, Cas. And, it sounds like you do too.”

Cas winked at him and their food arrived.

As they ate, they chatted about music, movies, and their mutual love of Dr. Sexy.

When they were done, Dean threw some money down on the table.

“Come on, Cas, I’ll drive you to your dorm.”

“I don’t live on campus, Dean. I’ve got a small apartment.”

“Well, give me the address then.”

Dean pulled up in front of a row of apartments and followed Cas to his door. Cas unlocked the door and turned around.

“Want to come in, have another beer?”

“I’d like that a lot, Cas.”

 


	2. Chapter 2

They sat together on the couch, sipping their beer.

“So, will you go out with me again?”

Cas grinned. “Trying to convince me that I won’t just be another notch on your headboard?”

Dean frowned. “I’m not like that, Cas. Just go out with me again.”

Cas’ eyes twinkled merrily. “Okay. As a man or a woman this time?”

Dean eyed Cas with a leer. “Your choice. Dancing. Tomorrow night.”

Cas tapped his chin thoughtfully with his index finger.

“I think I’ll go as a woman then.”

Dean’s pupils got dark. Cas laughed. “I can see you like that idea.”

Dean stood up. “I think I better be going, Cas. Thanks for going out with me tonight, and I’m really looking forward to tomorrow. Can I pick you up at ten?”

Cas stood up and walked with Dean to the door. “Sounds perfect. I’ll try to do you proud.” He leaned up and kissed Dean lightly.

“Oh, I’m sure you will do just fine. Good night, Cas.”

 

*****

 

Dean knocked on Cas’ door at exactly ten. He waited and then the door opened.

When he saw Cas, he gasped.

Cas was wearing a tight black dress, with black stockings and red high heels that made him as tall as Dean. His makeup was flawless but his dark hair was still the messy style that fitted him perfectly, either as a man or a woman.

“Damn, Cas. You look…”

Cas smiled. He twirled around. “I take it you like?”

Dean’s voice was a growl. “Yeah, I like.”

Cas grabbed a small bag. “Then, let’s go dance.”

 

*****

 

Dean guided Cas into the club. The music was loud and the dance floor was packed. They found a booth in the back where the music wasn’t quite as loud.

They both ordered a beer. Cas grabbed Dean’s hand.

“Let’s dance.”

Cas led Dean to the crowded dance floor and began to dance. He was very sensual, grinding up against Dean and moving his ass in a way that had Dean’s cock twitching in no time.

Thankfully for Dean, the next song was a slow one. He put his hands on Cas’ hips and pulled him close. Cas put his arms around Dean’s neck and his head on Dean’s shoulder.

Dean thought that Cas fit in his arms perfectly.

They swayed to the music. Dean leaned his head on top of Cas’ and sighed.

When the song was over, they went back to the booth to catch their breath and cool off. 

“Hey Dean! Who’s this pretty lady?”

Dean grinned. “Hi Benny. This is, uh… Cassie.”

Cas extended his hand. “Hi Benny. I’m Cas, Dean’s boyfriend.”

Dean chuckled and Benny opened his mouth, then closed it again.

“Uh… nice to meet you, Cas. Hey, I’ll… uh… I’ll see you around, Dean.”

Benny hurried away, and Dean burst out laughing.

“Cas, that was priceless.”

Cas grinned. “I appreciate you not outing me, but I don’t give a fuck. I hope you don’t mind”

Dean chuckled. “Mind? I loved it, Cas.”

They had a few more beers and danced some more, then Cas said he’d like to go home.

Dean walked him to the car, but when they got to it, Cas pushed Dean against the fender and kissed him. Dean grabbed Cas’ face in his hands and kissed him back. They stood for a few minutes, just kissing, until Cas broke away.

“Spend the night with me?”

Dean grinned. “There is nothing I’d like better than to spend the night with you.”

When they got inside Cas’ apartment, Cas grabbed Dean’s hand and led him to the bedroom. He paused, kissing Dean again, then he turned around.

“Unzip me?’

Dean grinned, putting on hand on Cas’ hip and grasping the zipper pull in the other. He pulled the zipper down slowly, taking in every inch of Cas’ skin as he did.

Dean slid the dress off of Cas’ shoulders and down his arms. Cas pulled it down and stepped out of it.

Dean bit his lip at the sight of Cas’ ass in panties, garter belt and the back of his bra. He ran his hands down Cas’ hips and Cas leaned back against him.

Dean turned Cas around and took in the sight. Cas had on a padded bra, red with black lace. His garter belt was also red with black lace trim. Dean sucked in a breath. 

“You look good enough to eat, Cas.”

Cas giggled and reached back to undo his bra, letting it fall down his arms. He let it fall to the floor, on top of the dress.

He stepped out of the high heels and kicked them aside. That left him wearing only the garter belt, panties and stockings.

Dean took a deep breath, pulling Cas to him. He kissed Cas passionately, then scooped him up and carried him to the bed.

Cas landed on the bed. “Oh, so strong, Mr. Winchester!”

Dean smiled at Cas and began to strip. Cas watched him intently. When Dean pulled off his boxers, Cas whistled.

“Very impressive.”

Dean crawled over him. “All the better to fuck you with, Red.”

Dean kissed along Cas' jaw and down his throat. Cas turned his head to give Dean all the access he wanted.

Dean worked his mouth down, sucking at each of Cas’ nipples. Cas moaned.

Dean then sat back on his heels and undid the garter belt, unhooking it from Cas’ stockings, pulling it from under Cas and tossing it aside. He smiled at Cas’ hard cock, peeking out of the top of his panties.

He leaned over and mouthed at Cas’ cock through his panties and Cas groaned again.

Dean pushed up on Cas’ ass and Cas lifted it in the air. Dean grabbed the panties and pulled them down. He yanked them off and tossed them aside.

Dean licked down the trail of dark fuzz that led from Cas’ navel to his cock. He kissed the tip of Cas’ cock.

“Lube?”

Cas turned his shoulders and grabbed a bottle from the bedside table, handing it to Dean. Dean poured some over his fingers.

Cas lifted his legs, bending them at the knee.

Dean slid one finger into Cas and Cas moaned. 

He slowly worked Cas open. They both were sweating and needy as hell.

When Dean couldn’t stand it anymore, he yanked his fingers out. Cas reached and threw him a condom, and Dean rolled it on.

“Ready, angel?”

 


	3. Chapter 3

“Oh god, Dean. Fuck me… please…”

Dean loved the low, gravely beg in Cas’ voice. He pushed his cock into the man and groaned at the feeling.

He pushed in all the way, then pulled back out. He looked down and pushed in again, loving the sight of Cas opening up for his cock. He did it a couple more times then established a hard rhythm.

Cas wrapped his legs around Dean’s hips and met every thrust with one of his own. 

Cas grabbed his cock and began to jerk it almost frantically. He was moaning and grunting with each thrust.

Dean kept up the hard thrusting until he felt his balls tighten. Then Cas came, shooting cum all over himself.

Dean yanked his cock out, rolled off the condom and came hard, all over Cas’ ass. 

He scooped up some of his cum on two fingers and pushed them inside of Cas’ hole, with Cas groaning at the feeling.

Dean crawled off the bed. “Bathroom?”

Cas pointed and Dean went and got a damp cloth to clean Cas off.

When he was done, he tossed the cloth to the floor and laid down next to Cas.

Cas cuddled up to him and laid his head on Dean’s shoulder.

“That was really amazing, Dean.”

Dean kissed the top of Cas’ head. “Yeah. Yeah, it really was.”

They had sex twice more that night. Each time was just as good as the first time for both of them.

Dean woke up and had no conception of what time it was. He looked at Cas, who was currently the little spoon to his big spoon.

Dean had to piss, so he got carefully out of bed, not wanting to wake up his sleeping beauty. He chuckled to himself at the term, but he really did think of Cas as a beauty.

He got back in the bedroom to find Cas was awake.

“Hey, angel, I’m sorry I woke you up.”

Cas smiled and pulled the covers back, inviting Dean back in. Dean got in and pulled Cas to him for a kiss.

“Why do you call me angel?”

Dean chuckled. “That’s what you are to me. You appeared in my life out of nowhere, then disappeared, made me look for you for weeks and then poof! You appeared again, just when I was losing faith.”

Cas looked puzzled. “Losing faith? In what?’”

“In ever finding you again, ever seeing you again.”

Cas kissed Dean tenderly. “That’s so sweet.”

Dean kissed him back. 

“So, what time is it? I’m starving.” Dean patted his stomach.

Cas grabbed his phone from the nightstand. “Almost noon. Let’s get something to eat.”

They walked to a little diner close to where Cas lived and ordered breakfast.

Cas sipped his coffee. “So, plans for the day?”

Dean grinned. “Well, I was hoping to spend the day with you. I mean, if that’s okay with you.”

Cas smiled that bright smile that seemed to light up every corner of the room.

“It’s more than okay!”

 

*****

 

They were naked in bed, and Dean was exploring every inch of Cas.

Dean nibbled down his neck, which made Cas giggle. Dean loved the sound.

He kissed over Cas’ chest, ran his hands down Cas’ arms and over his belly.

He lifted each leg and ran his hands over it, even looking at Cas’ toes.

“Fuck, you are so beautiful, Cas.”

Cas smiled down at him. “Have you taken a look in a mirror lately. You’re the beautiful one, wolfy.”

Dean pulled Cas up and embraced him. Cas wrapped his legs around Dean’s hips.

“I really like you, Cas.”

Cas pulled his head back to look in Dean’s eyes. “I like you too, Dean.”

Dean held him for a while. 

Then Cas’ phone began to chime with repeated text alerts. Sighing, Cas reached for the phone. When he looked at them, he frowned.

“Who is it?” Dean looked at the expression on Cas’ face.

“It says it’s from your friend Benny. How did he even get my number?”

“I have no idea.” Dean was frowning. “What is he saying?”

Cas looked upset. “He wants to know if I know where you are. He wants to come over. He wants…”

Dean was furious. “He wants what? Cas, tell me.”

Cas looked at Dean. “He says he wants a turn with me. He says I look sexy as a woman. Hot. He thinks I’d be really kinky in bed.”

Dean jumped up. “Where are my pants? I’m gonna kill him!”

Cas grabbed Dean’s arm. “Dean, no. Please, let it go. I get stuff like this all the time. I should know better than to crossdress in public.”

Dean turned to him. “What? Guys treat you like a slut because of that? That’s horrible. But Benny is supposed to be my friend. Give me your phone.”

Cas handed Dean his phone. He typed something into Cas’ phone and hit send.

A moment later, there was an alert. Cas looked at it.

“He says he’s sorry, Dean. He had no idea I was your… boyfriend? Is that what you told him? That we’re in a relationship?”

Dean grinned. “Of course. We are, aren’t we? I think I know when I’m in a relationship.”

Cas kissed Dean hard.

“See? I told you this wasn’t about just a one night stand, another notch in my headboard.”

Cas nodded and kissed Dean again.

They spent the rest of the day curled up on the couch together in their boxers, watching Netflix. They ordered pizza when they got hungry.

A little while later, Dean pulled Cas into his lap. Cas could feel how hard Dean was.

“Been sitting here thinking how much I want another piece of that beautiful ass.”

Cas jumped up, ran to the bedroom and was back in a flash, handing Dean the lube and a condom.

Dean frowned. “We need to get tested, I hate these things.”

Cas giggled. “Well, you wouldn’t want me to get pregnant, would you?”

Dean feigned shock. “What? I thought you were on the pill.”

In just a short time. Cas was sliding down on Dean’s cock and moaning.

 


	4. Chapter 4

From that weekend on, they were inseparable. They went out out once a month with Cas dressed like a woman. Dean adored it but if anyone hit on Cas, he put a stop to it immediately. He was very protective of Cas, and more than a little jealous as well.

Cas met Dean’s little brother (who, he pointed out, wasn’t so little after all) and Dean met Cas’ older brother. Everyone got along great.

After graduation. Cas got a job as an English teacher and Dean entered his master’s program. He worked part time as a mechanic to supplement their income. They got a small apartment near the college.

Dean graduated two years later, and got a job with the district attorney’s office. Cas wanted him to get his docortate but Dean said he’d had enough college for a lifetime.

Three months later, Dean proposed on Valentine’s day. They were married six months later.

Cas limited his crossdressing to their home, for Dean’s eyes only.

A year later they bought a house.

Two years later, they adopted a toddler named Jack. Cas quit his teaching job to stay home and take care of their son.

Cas limited his crossdressing to the bedroom after that.

They lived a long and happy life together. 

  
  
  
  
  
  



End file.
